Shelter Island Hotel Guide - Hotels with Pool in Shelter Island, New York

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Check availability on Shelter Island Hotels with Pool

Top Shelter Island Hotels with Pool

Outdoor pool, a heated pool
Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is €1,183
includes taxes & fees
23 Nov - 24 Nov
Work and Play Special! Extended Stay Discount
BBQ/picnic Area
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
9.4 out of 10, Exceptional, (69)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
The price is €130
includes taxes & fees
4 Dec - 5 Dec
Offshore Montauk
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (535)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is €146
includes taxes & fees
21 Dec - 22 Dec
The Harbor Front Inn
Seasonal outdoor pool
Clinton Motel

Clinton Motel

2.5 star property
Clinton
8.6 out of 10, Excellent, (293)
"Great staff and clean rooms"
United States
Tyler
The price is €78
includes taxes & fees
30 Nov - 1 Dec
Clinton Motel
Exterior
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is €154
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor
Seasonal outdoor pool, pool umbrellas, pool loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

2.0 star property
Culloden Shores
8.4 out of 10, Very good, (876)
"Very clean and spacious room! "
United States
Mary Beth
Kenny's Tipperary Inn
Property map
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is €174
includes taxes & fees
23 Nov - 24 Nov
North Fork Cottages & RV Resort
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (438)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is €87
includes taxes & fees
22 Nov - 23 Nov
Hamlet Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (382)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is €111
includes taxes & fees
30 Nov - 1 Dec
The Bentley Hotel Southampton
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
Old Saybrook
7.2 out of 10, Good, (459)
"🙂"
United States
Jared
The price is €71
includes taxes & fees
30 Nov - 1 Dec
Econo Lodge Inn & Suites Old Saybrook Westbrook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"amenities clean room with turndown service "
michael 2-night trip
Posted 6 days ago
Saybrook Point Resort & Marina

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Frequently asked questions

What are some accommodation options with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Features a seasonal outdoor pool, an indoor pool and a private beach. Pier Blue Inn Old Saybrook - Essex: Provides sunloungers, an indoor pool and complimentary wireless Internet access. Montauk Blue Hotel: Features buffet, an indoor pool and free self parking. Quality Inn Old Saybrook - Westbrook: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Features 2 outdoor swimming pools, an indoor pool and a full-service spa.
What is there to see and do in Shelter Island?
Surround yourself with nature at Sunset Beach and Crescent Beach. Discover sights such as Shelter Island Historical Society, Shelter Island Whale's Tail and Mashomack Preserve during your stay.
When is the best time to book a hotel with a pool in Shelter Island?
You may want to think about accommodation that has an outdoor pool if you'll be visiting Shelter Island in the hottest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be what you want if you come to town during the coldest months of January, February or March, when the average temperature is 3°C.